dirft84's definitions
the act of anal sex with a reluctant partner, wherein he or she demands compensation in the form of an extended holiday to a tropical destination.
Guy 1: "I haven't seen Eric in the office all week, what's up with him?"
Guy 2: "Oh yeah, I think he took his wife on a Jamaican Vacation."
Guy 2: "Oh yeah, I think he took his wife on a Jamaican Vacation."
by dirft84 February 3, 2010
Get the Jamaican Vacationmug.